


Planning Ahead

by orphan_account



Category: Supernatural
Genre: F/M, Language, mild violence
Language: English
Status: Completed
Published: 2018-12-18
Updated: 2018-12-18
Packaged: 2019-09-22 10:37:34
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,425
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17058224
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/orphan_account
Summary: Dean decides it’s time to give in…so he takes you out for a date, on Halloween.





	Planning Ahead

You expertly applied a bit of mascara and lipstick before you looked yourself over in the mirror.  Normally, you wouldn’t doll yourself up to go out.  You would just throw your hair in a ponytail and go.  But this time, you made sure your hair looked nice, pulled back in a French braid, had a little bit of make-up on, but not too much.  You had on your favorite pair of dark jeans and a black tank top.  Your boots were waiting for you over by the door…you looked good.  Which was good…because tonight was you and Dean’s first date.

 

You don’t know what finally made him want to take you out on the date.  You two had been dancing around each other for a while now, and it seemed like that was where it was going.  But it still took you by surprise when he came up to you yesterday and asked if he could take you out today…on Halloween. 

 

You heard a soft knock come from your door and smiled when you saw Dean standing there.  “Wow, you look beautiful!”  He said with a big smile on his face.  “Can I come in?” 

 

You returned his happy smile and nodded before walking over to him.  “What’s that?” 

 

Your eyes caught onto the site of Dean holding one of his red flannel shirts.  “Oh…well, it is going to be colder than I expected today, so I figured you could borrow it, to stay warm.”  He had this little smirk on his face that made him irresistible. 

 

“Thank you, Dean.”  You gave his cheek a little kiss before pulling the flannel up and onto your arms, wrapping it around your body.  You loved wearing Dean’s clothes, being wrapped up in his warmth and scent, it was intoxicating.  “So…where are we going?” 

 

“It’s a surprise!”  He laughed as he spoke.  You had been needling him for the past 24 hours, and now the time had finally come.  “Come on, I promise you will love it!”  Those green eyes bored into yours as he reached down and pushed against the small of your back, leading you out to the Impala.

 

000

 

“I don’t believe it!”  You giggled as you walked up to the entrance with Dean.  A few months ago, there was a hunt tied to an apple orchard, and you mentioned how you used to love to go to them when you were younger.  Apparently, Dean remembered.  “An Apple Orchard!” 

 

Dean chuckled at your enthusiasm, he always loved seeing your eyes light up when you got excited about something.  “You got it, sweetheart.  Just like you used to go to.  Why don’t we head in and have some fun?”  You nodded excitedly as Dean walked beside you to the entrance. 

 

Given that it was actually Halloween, there was a lot more to do.  They had a pumpkin carving station, hay rack rides, bobbing for apples, a haunted house.  All the things you loved about this season and holiday. 

 

“What first, sweetheart?”  Dean asked as he looked around.  You followed his eyes and saw it glance over a stand that said ‘Pie’, but he quickly turned his face back to you. 

 

Your eyes went wide at the realization…was Dean Winchester turning down pie…for you?  Oh, can’t have that…  “I was thinking…maybe we could split a slice of pie?  I am a little hungry.”  You gave him a wink, making his face turn a little red.  He knew you had caught him. 

 

The two of you ate slowly as you squeezed close together to share.  “Woah, this is the best pie, ever!”  Dean said with a deep moan as he took his first bite.  You could only laugh as you watched him.  It really was the little things in life that please Dean. 

 

000

 

“Oh, come on!  It will be fun!”  You tried again to convince Dean to bob for apples, but he wasn’t having it. 

 

“I’m not sticking my head in the water…it’s freezing out here.”  He gave you a playful glare before you smiled.

 

“Fine.  I guess I’ll do it on my own…”  You said with a smirk as you walked over to the booth.  The older gentleman smiled as you walked up.

 

“Ready to have a go?”  He asked you as he looked down to the big barrel full of apples. 

 

“Absolutely!”  You said with a giggle. 

 

The man got up and watched you as you leaned forward and tried to nip at the apples, hoping to catch one just right.  Every time you tried to grab one, it seemed just out of reach.  So you figured, go big or go home? 

 

So you picked and apple and just dove your face into the water, capturing it with your teeth before pulling back up.  The front of your hair was wet, so was your face, but for the most part, you came out pretty dry. 

 

You stood up proudly and looked to Dean with the apple still in your mouth, before taking the bite and tossing him the apple.  “Told you it wasn’t hard…” 

 

Dean took a bite of the apple as well as the man handed over a little cup of hot apple cider and key chain, your prize for getting an apple.  Dean hummed as you walked back over to him, sipping your drink, and you could have sworn he mumbled something like, “Oh, it’s hard alright.” 

 

000

 

“We hunt monsters for a living, we can handle a haunted house.”  Dean said as he walked up to the next attraction. 

 

It wasn’t that you were scared, you just…spooked easily.  Jump scares were especially bad.  “I don’t know Dean…” 

 

Dean turned and saw how you were biting your lip, like you always did when you got nervous.  How your eyes were turned down to the ground, like you always did when you were embarrassed.  “Hey…I’ll be right there the whole time.”  He said as he reached out and wove his fingers through yours. 

 

Your heart fluttered at the sudden contact, before you smiled and followed him into the front of the haunted house.  “I’ll keep you safe, I promise…”  Dean whispered into your ear as he gave you a quick kiss on the head. 

 

But it wasn’t you that Dean needed to keep safe…  Jump scares.  You hated them.  And for good reason.  Anyone who decides it’s a good idea to pull a jump scare on a hunter, gets what they deserve.  Which was why one of the scare-ers (scare people?) were now on their knees holding their nose after you punched them. 

 

“Son of a bitch!  I told you to stop!”  You screamed at the guy as he stood back up.  The man gave you a glare before stomping off to warn the others to keep their distance from you.

 

Dean was practically on the floor in laughter.  Honestly, when he went into the haunted house, he had hoped it would be an excuse for him to wrap you up in his arms, to hold you close.  And then maybe, when you got out of the other side, he would pull you close and kiss you.  But that wasn’t happening…because instead of jumping into his arms at every turn…you fought the fake monsters.

 

Sure, it ruined his plan…but it was the most badass, sexy, adorable thing he had ever seen.  When that ‘axe murder’ jumped around the corner, you let out a yelp, followed quickly by a right handed jab to the guys face.  You even managed to catch the fake axe and get into a defensive stance before he even hit the ground.

 

“It’s not funny, Dean.”  You tried to sound serious, but at the same time…it was kinda funny.

 

“Oh, man…I’m so glad we went on this date!  I can’t wait to tell Sam what just happened!”  Dean said as he straightened himself out and then quickly took up your hand in his again.  “So…I’m going to hold onto this…for everyone safety.” 

 

You giggled as you leaned against him and made your way through the rest of the attraction.

 

The day had been spent at little attractions, eating pie (four slices wasn’t much, was it?), and picking apples.  You and Dean were having a great time, sharing stories and funny moments.  You would cuddle up next to each other and hold hands, even share a couple of moments that you had hoped would lead to an actual kiss…but no dice yet. 

 

The sun was beginning to set as you pulled Dean’s flannel tighter around your shoulders.  The air was getting cooler as the sun went away.  Dean noticed you pull it tighter and smiled.  “One more thing, and then we will go?  There is something I want to do…” 

 

“Of course, Dean!”  You said excitedly.  You had done most of the things this place had to offer…what was left? 

 

Dean led you through the different people who were left, getting their last things before heading home.  He had actually called ahead and booked this little activity to be done in private, just the two of you, and he couldn’t wait. 

 

You turned the corner of the barn and smiled when you saw a tractor with a hay rack attached, with different hay bales and blankets over them.  “You Dean Winchester?”  The man said who was perched on the tractor.

 

You gave Dean a look as he nodded and then helped you onto the hay rack.  “Dean?  How does he know your name?”  You gave him a smirk, already having an idea in your mind. 

 

“No idea.”  He gave you a wink as he hopped up on the rack with you, sitting on the bale right next to you.  “We’re good to go!”  He shouted.

 

Before you could ask any other questions, the tractor roared to life and there was a little jolt before the rack began to move.  Dean squirmed a little as he got situated, pulling one of the blankets over to cover both of your laps with. 

 

You smiled at him as he looked down and then reached around your shoulders, letting you relax against him during the ride.  The smile on your face couldn’t be contained as you tucked your body against Deans, laying your head against his shoulder as his arm wound around your waist, his other hand coming up and wrapping around yours. 

 

“So…how did I do?  I don’t exactly do dates very often.”  Dean asked as the ride went through the orchard.  The light passed through the trees and gave off ambient light, making the green of Dean’s eyes really pop as you looked up to him with a smile.

 

“It’s perfect.”  You leaned forward and pressed your lips softly to Dean’s, taking in every moment of you and his first kiss.  The two of you stayed that way, sharing soft kissed for a while, before you felt the tractor begin to turn around for the last half of the ride. 

 

You snuggled against Dean as he wrapped you up in his arms for the ride back.

 

000

 

You stepped into the bunker and held open the door for Dean.  You don’t know how you came back with this much stuff…from an apple orchard no less.  You had five bags.  One was filled with apples that you picked.  One had a gallon of apple cider, two bags had pies…for a grand total of four pies, all different varieties on apple pie.  And the last one was a mystery.  It was a thin paper bag that Dean had been handed when you left the orchard…

 

“Dean, I can carry some of that…”  You offered again, but he just shook his head.

 

“I got it!”  He gave you a smiled before leaning over and capturing your lips with a kiss.  You couldn’t argue with that logic…

 

So the two of you made your way to the kitchen.  You turned the corner, walking in front of Dean, when you heard Sam call out to you, asking how the date went.  You smiled widely as Dean went into all the things you did, really having fun telling him how you decked that kid in the haunted house. 

 

Sam laughed along as you put all the goodies away, enjoying hearing about how you and Dean’s first date went well.  He knew the two of you were a match made in heaven, you both just needed to man, or woman, up and make a move. 

 

Sam snatched a couple apples up before leaving you alone with Dean.  “Okay, I need to know…”

 

Dean looked over to you for a moment and saw you point to the paper bag.  He smiled as he walked over to you and wrapped you up in his arms, pulling your back to his chest.  “Open it.”  He whispered into your ear before giving your neck a couple kisses. 

 

You hummed at his touch as you tilted the bag and out slid a few…photos?  You looked down as you saw different moments you shared with Dean.  The first was of you and Dean out in the orchard.  He lifted you up on his back to get a nice apple higher up. It was right after you grabbed it and he was looking up at you with a huge smile on his face, and yours.

 

The second was you leaning over at the bobbing for apples stand.  You barked out a laugh as you held it up and gave Dean a look.  “Now I have proof that you were checking out my ass!”  You giggled as he rolled his eyes with a smile.  You took in the moment…you really had never seen Dean smile so much.

 

With that thought, you turned back to the pictures and saw the last couple were of you and him on the hayrack ride.  One was of you two sharing a kiss, the other was of you two with the sunset in the background, cuddled up to each other. 

 

“Dean…”  You said as you turned in his arms.  “You had all of this planned ahead of time didn’t you?” 

 

He nodded as he smirked.  “Wish I would have known about you decking that guy…wish we could have gotten that picture.”  He mumbled as you playful slapped his chest. 

 

“You are perfect, Dean Winchester.” 

 

Dean smiled as he looked down at you and gave you a deep, passionate kiss, marking the end of your best first date, ever. 


End file.
